This can be a difficult thing to pin down and figure out.
We wont aim on the WHY so much, as we will concentrate on the FIX......if possible.
Something to keep in mind about this issue.....Outlook is a MICROSOFT application, and iCloud is an APPLE application.
Now we all know Apple and Microsoft are competitors, and only work together if there is MASS amounts of money to be made. Hence iCloud for Windows, and Outlook for mac (as examples)
We may come to the conclusion, that there is a bug that has YET to be vetted out, and will render this issue NOT FIXABLE.
With that said, I will do my absolute best, ***** ***** not give up, until I have bonafide proof, that sides on fixable or not.
So......lets do some initial troubleshooting first.
Turn iCloud Calendar, Contacts and Reminders off and back on
- Close Outlook.
- Open iCloud for Windows.
- Deselect the Mail, Contacts, Calendars & Tasks checkbox and click Apply.
- Wait a few seconds. Select Mail, Contacts, Calendars & Tasks, and click Apply.
- Open Outlook.